Southern Highlands Beach Vacations

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Top Beach vacation packages in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
Oaks Sydney Goldsbrough Suites

Oaks Sydney Goldsbrough Suites

Pyrmont
$1,354
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
8.2/10 Very Good! (7,771 reviews)
Staff

Reviewed on Sep 16, 2026

Pullman Sydney Hyde Park

Pullman Sydney Hyde Park

Darlinghurst
$1,739
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
8.6/10 Excellent! (1,001 reviews)
The location

Reviewed on Sep 12, 2026

Capella Sydney

Capella Sydney

Sydney Central Business District
$2,620
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
9.8/10 Exceptional! (410 reviews)
Attention to detail was amazing. Top service and spacious room.

Reviewed on Sep 6, 2026

Medusa Boutique Hotel

Medusa Boutique Hotel

Darlinghurst
$1,605
per person
Nov 5 - Nov 8
found 22 hours ago
Roundtrip flight included
Los Angeles (LAX) to Sydney (SYD)
9.6/10 Exceptional! (492 reviews)
This is the perfect hotel if you want a nice weekend away with your partner. Truly and unforgettable experience

Reviewed on Sep 11, 2026

The Capitol Hotel Sydney

The Capitol Hotel Sydney

Haymarket
$1,378
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
9/10 Wonderful! (1,004 reviews)
The location is fantastic and it’s very convenient to get to the attractions, very happy with our stay.

Reviewed on Sep 16, 2026

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5* Beach vacations in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
Pullman Sydney Hyde Park

Pullman Sydney Hyde Park

Darlinghurst
$1,739
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
8.6/10 Excellent! (1,001 reviews)
The location

Reviewed on Sep 12, 2026

Capella Sydney

Capella Sydney

Sydney Central Business District
$2,620
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
9.8/10 Exceptional! (410 reviews)
Attention to detail was amazing. Top service and spacious room.

Reviewed on Sep 6, 2026

The EVE Hotel Sydney

The EVE Hotel Sydney

Redfern
$2,963
per person
Dec 8 - Dec 13
found 4 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
9.8/10 Exceptional! (50 reviews)
Beautiful hotel with stylish interiors. It’s a shame however at the moment that they only have Olympus dining available as both Lottie and bar Julius are closed. It would also be great if you could order cocktails to the pool and not just a canned drink.

Reviewed on Sep 7, 2026

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3 Night Beach vacations in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
$1,079
per person
Nov 7 - Nov 8
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
8.2/10 Very Good! (2,903 reviews)
Great location, great service. Nice rooms!

Reviewed on Sep 16, 2026

Medusa Boutique Hotel

Medusa Boutique Hotel

Darlinghurst
$1,083
per person
Nov 7 - Nov 8
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
9.6/10 Exceptional! (492 reviews)
This is the perfect hotel if you want a nice weekend away with your partner. Truly and unforgettable experience

Reviewed on Sep 11, 2026

Establishment Hotel

Establishment Hotel

Sydney Central Business District
$1,085
per person
Nov 7 - Nov 8
found 8 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
9/10 Wonderful! (696 reviews)
We were welcomed by Emily at Front of House who was so helpful. She gave us great recommendations and really made us welcome. My only disappointment was due to booking through Expedia only 1 breakfast was included whereas if we had booked direct both guests would receive breakfast. Otherwise the stay was ideal. The area is great, 10 minute walk to most places, circular quay, the rocks, old sydney, the shopping area in Pitt Street.

Reviewed on Sep 7, 2026

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4 Night Beach vacations in Southern Highlands

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

Sydney Central Business District
$1,190
per person
Nov 9 - Nov 11
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Sydney (SYD)
8.4/10 Very Good! (1,000 reviews)
Very central location…staff were nice. But a few warning signs on the floors advising guests to respect others and keep quiet would have been good. Was not impressed with noisy guests on my floor with little self awareness.

Reviewed on Sep 11, 2026

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

Sydney Central Business District
$1,230
per person
Nov 9 - Nov 11
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Sydney (SYD)
8.6/10 Excellent! (1,004 reviews)
Staff was excellent

Reviewed on Sep 15, 2026

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
$1,201
per person
Nov 9 - Nov 11
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Sydney (SYD)
8.2/10 Very Good! (2,903 reviews)
Great location, great service. Nice rooms!

Reviewed on Sep 16, 2026

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Find your perfect Southern Highlands beach vacation

How do I book the best Southern Highlands beach vacation packages?

Life’s a beach when you dive into our brilliant Southern Highlands beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Southern Highlands?

A rental steps from the shore creates an amazingly affordable Southern Highlands beach vacation. Seaside sojourns during low season start from $1,079. Prices and availability are subject to change. Additional terms may apply.

When should I book a Southern Highlands beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

How can I book the best family beach vacations in Southern Highlands?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Southern Highlands beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Southern Highlands vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Southern Highlands beach vacation deals?

Sort your search results by deals to delight in amazing Southern Highlands beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Southern Highlands beach trip with free cancellation and/or flexible dates?

Just like the Southern Highlands tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Southern Highlands beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Southern Highlands. (OK, maybe not that last part.)

Top Beach Southern Highlands Hotels

French Boutique The Loft Apartment @Chapmans+Pets+B'fast

French Boutique The Loft Apartment @Chapmans+Pets+B'fast

Moss Vale NSW
  • 15 min drive from Bendooley Estate Book Barn
Book a stay at this golf apartment in Bowral. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Moss Vale Golf Club and Leighton Gardens are ...
8.4/10 Very Good! (7 reviews)
"The Loft area worked very well for us. Two travellers and a dog. The space was very clean, the beds very comfortable, the bathroom had a great shower with lots of hot water and my granddaughter enjoyed the seperate bath each of our 4 nights. It rained our entire time and I have to sincerely thank ..."

Reviewed on Jul 10, 2026

French Boutique The Loft Apartment @Chapmans+Pets+B'fast
5 star couples hideaway in the country, enjoy privacy and space - w hot tub

5 star couples hideaway in the country, enjoy privacy and space - w hot tub

Penrose NSW
  • 46 min drive from Bendooley Estate Book Barn
Stay at this cabin in Penrose. Enjoy free WiFi, a garden, and patios. Popular attractions Sylvan Glen Golf Course and Penrose Park are located nearby.
10/10 Exceptional! (11 reviews)
"Was an amazing place! Perfect in all aspects!"

Reviewed on Apr 7, 2026

5 star couples hideaway in the country, enjoy privacy and space - w hot tub
The Coach House at The Rift Estate

The Coach House at The Rift Estate

Bowral NSW
  • 12 min drive from Bendooley Estate Book Barn
Book a stay at this family-friendly vacation home in Bowral. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Southern Highlands Botanic ...
9.8/10 Exceptional! (10 reviews)
"Fire Place was warm. The number of rooms were perfect for our extended family. Kitchen was well-equipped. The gardens and grounds were lovely"

Reviewed on Apr 13, 2026

The Coach House at The Rift Estate
See all 1,641 properties in Southern Highlands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

Sydney Wine Tasting & Southern Highlands with Pick up & drop off

Sydney Wine Tasting & Southern Highlands with Pick up & drop off

$325
per adult
Sydney Wine Tasting & Southern Highlands with Pick up & drop off
See all activities in Southern Highlands

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.